EP0354508A3 - Benzopyranol derivatives - Google Patents

Benzopyranol derivatives Download PDF

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Publication number
EP0354508A3
EP0354508A3 EP19890114523 EP89114523A EP0354508A3 EP 0354508 A3 EP0354508 A3 EP 0354508A3 EP 19890114523 EP19890114523 EP 19890114523 EP 89114523 A EP89114523 A EP 89114523A EP 0354508 A3 EP0354508 A3 EP 0354508A3
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EP
European Patent Office
Prior art keywords
lower alkyl
alkyl
alkoxy
alkanoyl
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19890114523
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German (de)
French (fr)
Other versions
EP0354508A2 (en
Inventor
Armin Walser
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of EP0354508A2 publication Critical patent/EP0354508A2/en
Publication of EP0354508A3 publication Critical patent/EP0354508A3/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Obesity (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Benzopyranolderivate der Formel worin A -C≡C-R⁶, -CH₂CH₂-R⁷ oder und R¹ Wasserstoff oder nieder-Alkanoyl,
R², R³ und R⁴ Wasserstoff oder nieder-Alkyl,
R⁵ nieder-Alkyl,
R⁶ und R⁷ ein heteroaromatisches Radikal oder ein aromatisches Radikal aus der Gruppe von Phenyl, Naphthyl oder Phenanthryl, wobei ein solches aromatisches Radikal R⁶ oder R⁷ unsubstituiert oder durch einen oder mehrere Reste Z⁶ bzw. Z⁷ substituiert sein kann,
Z⁶ Phenyl-nieder-alkoxy, Hydroxyimino-nieder-alkyl oder eine Gruppe Z,
Z⁷ Phenyl-C₂₋₇-alkoxy oder eine Gruppe Z, Z, Cl, F, nieder-alkyl, nieder-Alkoxy, nieder-Alkanoyl, nieder-Alkanoyloxy, Hydroxy-nieder-alkyl, COOH, nieder-­ Alkoxycarbonyl, NH₂, Amino-nieder-alkyl, Mono- oder Di-nieder-alkylamino, Mono- oder Di-nieder-alkylamino-­ nieder-alkyl, nieder-Alkanoylamino, CONH₂, Mono- oder Di-nieder-alkylcarbamoyl, Trifluoracetylamino, CF₃, OH oder Pyridyl ist; oder Z mit zwei benachbarten C-Atomen die Gruppierung -OCH₂CH₂N(R″)- oder -OCH₂CON(R‴)- bildet,
R″ H, nieder Alkanoyl oder Trifluoracetyl,
R‴ H oder nieder Alkyl,
R⁸, R⁹ und R¹⁰ H, OH, nieder Alkyl, nieder Alkoxy, Hydroxy-nieder-alkyl, F, Cl oder nieder-Alkanoyl sind, jedoch nicht mehr als eins von R⁸, R⁹ oder R¹⁰ OH, nieder-Alkoxy, Hydroxy-nieder-alkyl, F, Cl oder nieder-­ Alkanoyl ist, und
Y CH oder N ist,
und Salze davon. Benzopyranol derivatives of the formula wherein A -C≡C-R⁶, -CH₂CH₂-R⁷ or and R¹ is hydrogen or lower alkanoyl,
R², R³ and R⁴ are hydrogen or lower alkyl,
R⁵ lower alkyl,
R⁶ and R⁷ are a heteroaromatic radical or an aromatic radical from the group of phenyl, naphthyl or phenanthryl, where such an aromatic radical R⁶ or R⁷ may be unsubstituted or substituted by one or more Z⁶ or Z⁷ radicals,
Z⁶ phenyl-lower alkoxy, hydroxyimino-lower alkyl or a group Z,
Z⁷ phenyl-C₂₋₇-alkoxy or a group Z, Z, Cl, F, lower alkyl, lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy lower alkyl, COOH, lower alkoxycarbonyl, NH₂, amino -Lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino- lower alkyl, lower alkanoylamino, CONH₂, mono- or di-lower alkylcarbamoyl, trifluoroacetylamino, CF₃, OH or pyridyl ; or Z forms the grouping -OCH₂CH₂N (R ″) - or -OCH₂CON (R ‴) - with two adjacent C atoms,
R ″ H, lower alkanoyl or trifluoroacetyl,
R ‴ H or lower alkyl,
R⁸, R⁹ and R¹⁰ are H, OH, lower alkyl, lower alkoxy, hydroxy lower alkyl, F, Cl or lower alkanoyl, but not more than one of R⁸, R⁹ or R¹⁰ OH, lower alkoxy, hydroxy lower -alkyl, F, Cl or lower alkanoyl, and
Y is CH or N,
and salts thereof.

Die Verbindungen der Formel I sind als Inhibitoren der 5-Lipoxygenase und der Lipidperoxidation wirksam. Sie sind daher bei der Behandlung von Krankheiten, die durch über­ mässigen oxidativen Metabolismus der Arachidonsäure via 5-Lipoxygenase verursacht sind, sowie bei der Behandlung von Inflammationen, Arthritis, Allergien, Asthma und Psoriasis von Wert. Die Verbindungen der Formel I können auch zur Vorbeugung der Peroxidation der Lipide und daher zum Schutz der Lipidmembranen gegen oxidative Beanspruchung Verwendung finden. The compounds of formula I are as inhibitors of 5-Lipoxygenase and lipid peroxidation effective. you are therefore in the treatment of diseases caused by over moderate oxidative metabolism of arachidonic acid via 5-Lipoxygenase are caused, as well as in the treatment of Inflammation, arthritis, allergies, asthma and psoriasis of value. The compounds of formula I can also Prevention of lipid peroxidation and therefore protection the lipid membranes against oxidative stress use Find.

Sie können hergestellt werden ausgehend von Verbindungen der Formel I, worin A für Aethinyl steht. They can be made from connections of formula I, wherein A is ethynyl.

EP19890114523 1988-08-09 1989-08-07 Benzopyranol derivatives Withdrawn EP0354508A3 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US23009488A 1988-08-09 1988-08-09
US230094 1988-08-09
US07/367,082 US5015661A (en) 1988-08-09 1989-06-16 Chromanes and their pharmaceutical compositions and methods
US367082 1989-06-16

Publications (2)

Publication Number Publication Date
EP0354508A2 EP0354508A2 (en) 1990-02-14
EP0354508A3 true EP0354508A3 (en) 1991-03-27

Family

ID=26923917

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19890114523 Withdrawn EP0354508A3 (en) 1988-08-09 1989-08-07 Benzopyranol derivatives

Country Status (13)

Country Link
US (1) US5015661A (en)
EP (1) EP0354508A3 (en)
JP (1) JPH0283379A (en)
KR (1) KR900003175A (en)
AU (1) AU616039B2 (en)
DK (1) DK389089A (en)
HU (1) HU206204B (en)
IL (1) IL91245A0 (en)
MC (1) MC2050A1 (en)
NO (1) NO172643C (en)
NZ (1) NZ230233A (en)
PH (1) PH27235A (en)
PT (1) PT91400A (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1305480C (en) * 1987-03-20 1992-07-21 Roshantha A.S. Chandraratna Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity
FR2676056B1 (en) * 1991-05-03 1993-07-16 Adir NOVEL BENZOPYRAN DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
US5149703A (en) * 1991-09-06 1992-09-22 Merck Frosst Canada, Inc. Quinoline-substituted chromans and related compounds as leukotriene antagonists
US5280040A (en) * 1993-03-11 1994-01-18 Zymogenetics, Inc. Methods for reducing bone loss using centchroman derivatives
US5451603A (en) * 1993-03-11 1995-09-19 Zymogenetics, Inc. 3,4-diarylchromans for treatment of dermatitis
CA2153979C (en) * 1993-12-08 2003-10-21 Mark Hellberg Compounds having both potent calcium antagonist and antioxidant activity and use thereof as cytoprotective agents
US5747528A (en) * 1996-02-21 1998-05-05 Warner-Lambert Company Chroman derivatives as anti-oxidants
ITTO20030140U1 (en) * 2003-09-16 2005-03-17 Interfila Srl COSMETIC PENCIL
CA2580584C (en) 2003-09-19 2015-07-28 Galileo Pharmaceuticals, Inc. Use of alpha-tocotrienol for treatment of mitochondrial diseases
BRPI0519013A2 (en) * 2004-12-13 2009-11-03 Lilly Co Eli single compound or stereoisomers, mixtures of pharmaceutically acceptable stereoisomers, salts, tautomers or prodrugs thereof, pharmaceutical composition, and use of a compound
CA2600004A1 (en) 2005-02-25 2006-09-08 Eli Lilly And Company Spiro-heterocyclic chromans, thiochromans and dihydroquinolines

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987005020A1 (en) * 1986-02-21 1987-08-27 Kuraray Co., Ltd. 3,4-dihydro-2h-benzopyran derivatives and their medicinal use
EP0320777A2 (en) * 1987-12-18 1989-06-21 F. Hoffmann-La Roche Ag A novel approach to produce natural vitamin E making use of an asymmetric synthesis
EP0207581B1 (en) * 1985-02-26 1990-09-12 Sankyo Company Limited Thiazolidine derivatives, their preparation and use

Family Cites Families (13)

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JPS6051189A (en) * 1983-08-30 1985-03-22 Sankyo Co Ltd Thiazolidine derivative and its preparation
US4681890A (en) * 1984-10-30 1987-07-21 Kuraray Co., Ltd. 3,4-dihydrobenzopyran compounds and pharmaceutical composition containing the same
DE3484473D1 (en) * 1984-12-06 1991-05-23 Kuraray Co CHROMAN CONNECTIONS AND THEIR PRODUCTION.
JPS61148173A (en) * 1984-12-20 1986-07-05 Kuraray Co Ltd Novel amine and its salt
JPS61204122A (en) * 1985-03-07 1986-09-10 Kuraray Co Ltd Remedy for liver disease
JPS61210030A (en) * 1985-03-13 1986-09-18 Agency Of Ind Science & Technol Antitumor agent
JPS61267571A (en) * 1985-05-20 1986-11-27 Kuraray Co Ltd 2-(4-chlorophenoxy)-2-methylpropionic acid ester and antilipemic agent containing said compound as active constituent
JPS61267570A (en) * 1985-05-20 1986-11-27 Kuraray Co Ltd 3,4-dihydro-2h-benzopyran derivative and cholagogue containing said derivative as active constituent
JPS62132879A (en) * 1985-12-05 1987-06-16 Kuraray Co Ltd 3,4-dihydro-2h-benzopyran derivative and antiallergic agent containing said derivative as active ingredient
US4752646A (en) * 1986-01-23 1988-06-21 Hoffmann-La Roche Inc. 2-halochromans
US4824971A (en) * 1986-01-23 1989-04-25 Hoffman-La Roche Inc. 2-allylchromans
US4879395A (en) * 1987-03-27 1989-11-07 Hoffmann-La Roche Inc. Vitamin E intermediate
US4914217A (en) * 1987-12-18 1990-04-03 Hoffmann-La Roche Inc. Asymmetric synthesis of natural vitamin E

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0207581B1 (en) * 1985-02-26 1990-09-12 Sankyo Company Limited Thiazolidine derivatives, their preparation and use
WO1987005020A1 (en) * 1986-02-21 1987-08-27 Kuraray Co., Ltd. 3,4-dihydro-2h-benzopyran derivatives and their medicinal use
EP0320777A2 (en) * 1987-12-18 1989-06-21 F. Hoffmann-La Roche Ag A novel approach to produce natural vitamin E making use of an asymmetric synthesis

Also Published As

Publication number Publication date
NZ230233A (en) 1992-03-26
HUT52493A (en) 1990-07-28
JPH0579072B2 (en) 1993-11-01
NO893198L (en) 1990-02-12
EP0354508A2 (en) 1990-02-14
NO893198D0 (en) 1989-08-08
KR900003175A (en) 1990-03-23
NO172643C (en) 1993-08-18
HU206204B (en) 1992-09-28
AU616039B2 (en) 1991-10-17
PH27235A (en) 1993-05-04
NO172643B (en) 1993-05-10
MC2050A1 (en) 1990-07-17
US5015661A (en) 1991-05-14
PT91400A (en) 1990-03-08
IL91245A0 (en) 1990-03-19
JPH0283379A (en) 1990-03-23
DK389089A (en) 1990-02-10
DK389089D0 (en) 1989-08-08
AU3941889A (en) 1990-02-15

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